Search Vacation Homes in Ashland

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Compare 285 Vacation Homes in Ashland with updated reviews, rates, and availability.

ZZ ZANY ZOO II - Townhome, with Carport & Garage

10.0 out of 10, Exceptional, (80)
"Adorable family-friendly theme with holiday spirit made for a memorable vacation."
ZZ ZANY ZOO II - Townhome, with Carport & Garage

Quiet and peaceful cottage close to downtown

9.8 out of 10, Exceptional, (50)
"Plants, 70s vinyl, a few antiques, nicely updated, clean, private backyard, good location, did I mention 70s vinly"
The price is SAR 694
SAR 1,242 total
includes taxes & fees
1 Apr - 2 Apr
Quiet and peaceful cottage close to downtown

New house with king beds and 3 full bathrooms

9.4 out of 10, Exceptional, (29)
"I will be staying here every time I come to Medford. "
The price is SAR 559
SAR 1,076 total
includes taxes & fees
6 Apr - 7 Apr
New house with king beds and 3 full bathrooms

Charming home, w/hot tub, close to downtown Pet-Friendly!

10.0 out of 10, Exceptional, (34)
"super cool"
The price is SAR 1,032
SAR 2,271 total
includes taxes & fees
1 Apr - 2 Apr
Charming home, w/hot tub, close to downtown Pet-Friendly!

The Original ZZ ZANY ZOO Townhome, with Carport & Garage #1

10.0 out of 10, Exceptional, (181)
"Beautiful cozy place to spend your time away from home. "
The Original ZZ ZANY ZOO Townhome, with Carport & Garage #1

Tastefully remodeled 3 bedroom 2 bath home with large private back yard

10.0 out of 10, Exceptional, (37)
"I normally stay in the same house when I drive through Medford in the winter but luckily it was booked and I found this gem! Pet friendly and accommodating owners. Loved the pet stairs for the bed access! So much so that I’m buying a set for myself …. Well for my dog. Thank you "
The price is SAR 675
SAR 1,473 total
includes taxes & fees
1 Apr - 2 Apr
Tastefully remodeled 3 bedroom 2 bath home with large private back yard

Large Private Carriage-House Retreat with Amazing Views

10.0 out of 10, Exceptional, (119)
"Really nice property in east Medford. It's pretty big and comfortable. Elyse has been hosting for a while and has done a nice job with it. She knows what she's doing.I come to Medford a few times a year and will definitely be back."
Large Private Carriage-House Retreat with Amazing Views

Great, clean house in the middle of Medford

9.2 out of 10, Wonderful, (44)
" Nice house. "
The price is SAR 488
SAR 1,207 total
includes taxes & fees
1 Apr - 2 Apr
Great, clean house in the middle of Medford

Cedar Wood Mountain View Retreat

10.0 out of 10, Exceptional, (3)
"We rented the house during Christmas break and it was absolutely wonderful for our large family. Everyone had enough sleeping space, the house was clean, cozy, and welcoming. The view of the mountains and countryside is also a plus! Everything worked out - and the hot tub was a nice addition. The house is even stocked with toys and books for children and plenty of towels and linens. We enjoyed cooking in kitchen as well. This is a great spot! "
Cedar Wood Mountain View Retreat

Three bedroom with king beds, 2 & a half bathroom. 2146 square foot house.

9.6 out of 10, Exceptional, (39)
"House was amazing, stayed with family and new grand baby. Everything you could need and the split level was perfect for us! Definitely will rent again next time were in Medford. "
Three bedroom with king beds, 2 & a half bathroom. 2146 square foot house.

Comfy Cozy Casa

10.0 out of 10, Exceptional, (42)
"We loved staying here! Our daughter and her family live here, but when we stay with them, one of our grandchildren have to give up their bed. This place was close to them and everything we needed, so it was perfect. The only downside was it snowed for a couple of days, but we stayed nice and cozy here. Will definitely come back! Thank you!"
The price is SAR 338
SAR 933 total
includes taxes & fees
1 Apr - 2 Apr
Comfy Cozy Casa

Sun Cottage Downtown Jacksonville

10.0 out of 10, Exceptional, (15)
"A little noisy with traffic, but the location was perfect. The lighting and ventilation in the kitchen was not the best, but throughout the rest of the house was great. Unfortunately, we burnt a little bit of our dinner and the smoke alarm went on (which was good) but we couldn't turn it off. Otherwise, great place and I would consider returning again."
The price is SAR 604
SAR 1,192 total
includes taxes & fees
1 Apr - 2 Apr
Sun Cottage Downtown Jacksonville

Peaceful, spacious home on 8 acres. Pet-friendly, close town, and a creek!

10.0 out of 10, Exceptional, (9)
"Nice quiet place just minutes away from Ashland. "
Peaceful, spacious home on 8 acres. Pet-friendly, close town, and a creek!

Cozy creekside home with deck, 15 min to airport, shopping, 1 hr to Crater Lk.

10.0 out of 10, Exceptional, (10)
"We loved this place. It was a special time for us, visiting family (including a very ill grandparent) over christmas. This wonderful riverside home was fantastic to come back to. No complaints whatsoever. The host was great, communication was great. We are incredibly grateful. Honestly, it was likely because of what we were going through, but this house felt a bit magical to us. A sanctuary. What a blessing."
Cozy creekside home with deck, 15 min to airport, shopping, 1 hr to Crater Lk.

Cozy, dog-friendly 3-bedroom fully stocked home in Medford with AC, WiFi

9.8 out of 10, Exceptional, (8)
"My family loved your home…me too! All of the extra goodies for the dog and them were very appreciated. Thank you Amanda for having this be a Wonderful place to visit!"
The price is SAR 600
SAR 1,127 total
includes taxes & fees
6 Apr - 7 Apr
Cozy, dog-friendly 3-bedroom fully stocked home in Medford with AC, WiFi

Beautifully Renovated Sleeps up to 8 in East Medford

Beautifully Renovated Sleeps up to 8 in East Medford

Ashland Lodge w/ Lake Views & Game Room Loft

10.0 out of 10, Exceptional, (68)
"Our family and friends had the best time. Would recommend to anyone that is looking for some peace and quiet. "
Ashland Lodge w/ Lake Views & Game Room Loft

Spacious contemporary home nestled in the foothills of RoxyAnn.

10.0 out of 10, Exceptional, (18)
"Place was great. Don’t need all the vrbo email."
Spacious contemporary home nestled in the foothills of RoxyAnn.

Beautiful Luxury Cottage. Walk To It All!

10.0 out of 10, Exceptional, (116)
"Upon entering the home, we were greeted with Christmas music, heated rooms, and snack treats. Jackie was always quick to respond to our few questions and had provided lots of information about the area. We spent our days exploring Jacksonville and Ashland, and the location of the house made this so convenient. We were able to take an evening walk to enjoy the Christmas lights in town and the neighborhood. Such a wonderful stay! We will certainly stay here again."
Beautiful Luxury Cottage. Walk To It All!

Main Residence: 5 beds, 5 baths, sleeping porches, & full kitchen.

9.6 out of 10, Exceptional, (5)
"Our family of 10, parents, their children and grandchildren, came to spend the holidays together. We had a great time in a fabulous property with plenty of room to all gather for meals and games or have some quiet time in our own space. Everyone enjoyed the adjacent coffee shop and tasting room complete with games. Several close options for hiking and groceries were just a mile or two away."
The price is SAR 1,684
SAR 3,278 total
includes taxes & fees
1 Apr - 2 Apr
Main Residence: 5 beds, 5 baths, sleeping porches, & full kitchen.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Don't see what you're looking for?
See all available properties in Ashland
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Ashland

A Cowslip's Belle Inn

3.0 star property
9.8 out of 10, Exceptional, (30)
"Lovely place and the room had everything I needed. "
The price is SAR 563
SAR 837 total
includes taxes & fees
6 Apr - 7 Apr
A Cowslip's Belle Inn

East Main Downtown Bungalow

9.4 out of 10, Exceptional, (25)
"We really enjoyed our short stay here! The cottage is clean, in a great location for walking to OSF and great food, and in a good neighborhood. Communication with the owner/manager was very easy and they were responsive to our few questions. We hope to return in 2025 for a longer visit!"
The price is SAR 488
SAR 983 total
includes taxes & fees
1 Apr - 2 Apr
East Main Downtown Bungalow

Ashland Lodge w/ Lake Views & Game Room Loft

10.0 out of 10, Exceptional, (68)
"Our family and friends had the best time. Would recommend to anyone that is looking for some peace and quiet. "
Ashland Lodge w/ Lake Views & Game Room Loft
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.